From the heavy to the light-hearted, the Today co-anchor has covered two decades worth of topics with Hollywood's biggest names—many times at their most critical career moments.

Whether it was Ryan Lochte at the height of international criticism or Kim Kardashian speaking for the first time about Caitlyn Jenner's transition, the 59-year-old journalist has proven time and time again he's not afraid to ask the difficult questions.

Today, on the 20th anniversary of landing the job, it was only fitting that we conjure up the most unique, at times tense and overall memorable star sit-downs with Lauer. Action!

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Most recently, the journalist faced the Olympic swimmer in August after his robbery scandal that had rocked Rio and temporarily halted his teammate's return to the United States. During the lengthy sit-down, Lauer wasted no time getting to the truth of Lochte's lies.

"I'm taking full responsibility for it because I over-exaggerated that story and if I [had] never done that, we wouldn't be in this mess," Lochte admitted.

"I'm embarrassed for myself, my family—especially those guys," he added tearfully. "I was immature and I made a stupid mistake. I'm human. I made a mistake and I definitely learned from this."

In 2012, the star was newly single after divorcing Marc Anthony. Lauer didn't avoid the subject, turning the conversation to the exes' continued professional partnerships and the end of their marriage. He did his homework, reading her previous quotes from Vanity Fair back to her and asking for further explanation. Lopez held her ground, but didn't hide the fact that she was caught off guard about being grilled.

"Matt, I want to kill you right now!" she joked as she hit him on the knee. "I'll punch you again!"

Charlie Sheen

After endless rumor and speculation, the Two and a Half Men star took a seat across from Lauer in 2015 to make a major personal announcement.

"I'm here to admit that I am in fact HIV-positive," the star explained on the morning show. "I have to put a stop to this onslaught, this barrage of attacks and of sub-truths and very harmful and mercurial stories that are about me, threatening the health of so many others, which couldn't be further from the truth."

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Of his many celebrity chats, there's arguably no exchange more famous thus far than the one he had with the War of the Worlds star in 2005. Upon a heated discussion about psychiatry and postpartum depression treatment, the actor called the journalist "glib" and the quip become infamous.

Three years later, they arm wrestled and had a truce in the same studio. "I thought about it a lot," Cruise told Lauer in 2008. "It's a subject matter that was important. After looking at it, I really thought, it's not what I had intended. In looking at myself, I came across arrogant. I absolutely could have handled that better."

Kim Kardashian

On the heels of Caitlyn Jenner's transition announcement, Lauer sat down with the reality star to get her first public, poignant reaction on the news.

"Say what you want about us, but we work out everything as a family and we have the best communication and we are so in sync with each other," she candidly told him. "We have each other to go through this experience with and I'm really grateful for that."